I know this photo is over at Men.Style.com but it is easily my favorite look of the season.

I love the formality of the DB with the worn jeans and velvet slippers. The shape of the DB is perfect.

This is a really inspiring image to me, not because I would want to wear the exact same thing – but it makes me think of how I would do it slightly differently and with the clothes I already have in my closet.

I have a navy cashmere single-breasted jacket, similarly worn jeans and brown slip-on loafers – I already own these elements, I just haven’t put them together quite this way.

It sounds so simple, but when you have a busy life you often just grab the looks that you already know work for you. Little visual reminders like this help me to mentally reorganize my closet.

Comments

This is indeed a good look. I picked up a pair of Bally suede slippers like the ones you show here, and I have paired them with jeans before. It is a bit of a precious look- not one to go slumming, but it is a good combination, especially when you want to dress up your jeans. I remain skeptical of the DB jacket, but it works on this guy as he appears to be slim. Love the tote, have to start saving for the Hermes one! Jorge from W Palm Beach

He has rolled his jeans perfectly – I mean perfectly. Length, cuff size, the leg of the pant is ideal, etc. I really like this look, I think he carries it off well. If his hair was less styled, it would make the entire presentation a little sexier.

What a great unexpected shot. This gentleman must be a character- probably even more interesting than his outfit. I think the jeans had to be this outrageously worn (and repaired- that matters to the look, as well)to work this perfectly. Like you I’d have to interpret the inspiration rather than copy the look. No velvet slippers, for example. Like the rolled cuffs, particularly the sleeves.

Sorry, but to me this has a “just fled a house fire” look — beautiful jacket, tattered jeans, slippers, no socks, as though all were grabbed in haste. Nope, not working together at all. With nice, deep indigo jeans, not rolled up, and leather loafers, maybe.

I’m surprised because I usually agree with you but this look I don’t like at all.First of all I cannot stand skulls anymore, and then the jeans don’t look like they’ve been worn for years but much more like he just bought them yestersay looking like this. To me it doesn’t look effortless at all but rather “nouveau-riche”.I see your point in taking the inspiration in general though.

Euh, well…It’s a little too american for me.I don’t like the artificially used jeans.I don’t like his haircut.I don’t like this agressively wealthy but casual anyway style. It’s a caricature, like if some RL advert had came (come ?) to life.

I do think there is fine line between fabolousity and trying too hard — but this one really goes over — sorry, though, of course, I appreciate the effort — but it just appearas too perfect and studied and styled and thought out — I mean, EVERYTHING is done just so — the pocket square, the upturned sleeve, the rolled up cuff, the clean white white tote –and the hair do — very “don’t touch the hair,”. I agree about the comment about the skulls — they were cool only when they first came out a couple of years — and only then for a couple of months. And I do have to say — the preppie motif — while a classic style (though I think rather too 20th century) — appears to age one unnessarily — he actually appears in his 50′s at first glance.

In general, double-breasted blazers seems to inspire extreme feelings. I am in the pro-DB camp.

As for the jeans pictured here, well, not so much . . . but i do like the idea of pairing a DB with pairing respectable jeans (I know, i am hopelessly fuddy duddy…but i never took a cotton to ripped and stained jeans) And I like socks too.

To the gentleman pictured here: Bravo for the proof-of-concept. Also, extra points awarded for the rolled up cuffs — panache personified!

I have been doing the same thing with the pictures on your site since I found it! You, and the people you shoot, brought me out of a total rut and back into my confidence. I love this site, my friend Rachel and I come here often. Thank you and keep up the fabulous work!

The guy in the trench coat is saying to himself “damn, He looks better with the cuff jeans, then I do :( ” I think the look is cool. The small touches- the pocket square, the tote and the slippers make the look different and that’s why he pulls it off.

Love the point about having little visual reminders to “mentally reorganize” your closet. I find that this blog does that. If a look posted resonates with me I try to see what I have to replicate it.

As for this look I have been imaging the same but a female version. I’ve got loads of wonderful blazers and jackets that I’m beginning to look forward to wearing now that nights are chilly. I’ll do flats but also something with a heel. Jeans will be the real deal patched up LEVI’s that got for $1 at a yard sale.

I like your comment, Sart. What i like best about this gentleman’s ensemble is his pink gingham shirt – or at least i think it’s pink gingham, i hope so! As for re-organising one’s closet, I am in England temporarily and my fall clothes are in lower manhattan. I’ve been in the attic going through things i wore 10 or more years ago to see what i can make work for me now. It’s been an interesting exercise and saved me some money too…

Technically this man should know exactly what he is doing since he’s the SVP of Men’s Design at Polo. The look is successful enough, but the jeans are a little too tattersol for my taste – he could’ve protrayed this message in a less aggressive way. And I’ve always detested those funny velvet (although, if they are from the Rugby line, they’ll be cotton velveteen) slippers. I like the blazer and shirt though…and this guy is a funny character overall personality wise…

I too am in the same boat as anne – surprised at my disappointment at this shot, as I’m normally in full agreement with you on style – perhaps because you can make even quite uncanny outfits seem beautiful in their own way.

But this ensemble is beyond rescue – it looks overdone and underdone at the same time and has a tasteless pretentiousness about it that just makes me cringe. The double-breasted jacket with gold buttons and pocket kerchief is much too formal, whereas the loafers look like house-shoes. The jeans do indeed seem to have been bought just yesterday. To top it all off the little over-groomed details – the slightly upturned jacket-cuffs, the slicked back hair – betray an all too deliberate casualness, a stiff attempt at frivolity.

anne @ 10:31 AM: “the jeans don’t look like they’ve been worn for years but much more like he just bought them yesterday looking like this. To me it doesn’t look effortless at all but rather “nouveau-riche”.”

That says it all. The proportions of the jeans look great, but the inauthentic feel to the wear pattern irritates me.

Trying to mix the clothes you already have in a diferent way is a very good exercise… However, I live in such a hurry that I usually wear them always the same… This guy must have choosen this look after a rainy day at home, pacticing the hi-lo exercise.. worn jeans + double breasted jacket + loafers ( to add a little fun..).

sart, you are dead on with your comment. lately i’ve been in the same state of mind. i have so many clothes over years and years that lately when i see something i like, i realize that purchasing it would be redundant. so what i’ve started doing is wearing the pieces that i have differently. here in dc, it’s been getting cool but still good for shorts, so i’ve been breaking out the cardigan and pairing them with shorts and loafers and things like that.

Everything’s fine, til we get down to the hem of the blazer. Then come the torn jeans flared and rolled up, the bare ankles over the pirate motif bedroom slippers, the spiffy tote bag… Sorry, but–yish! It’s not the concept of blazer with jeans and loafers: it’s just that the pieces on bottom side are so ugly! The only redeeming value is what you point out, a nudge to refresh an old wardrobe.

i will never understand the desire for buying brand new denim that look terribly inauthentic and “old”. there is something to be said for things that are worn, and mostly it comes form being, well, worn.

I love the look, minus the overdone jeans. I will certainly wear a version of this, but it is unfortunate that at my age (23) I will have to endure endless odd glances and snickering when going out in public – you get that even with a bold pocket square or seersucker in this town. Would that my city took fashion a bit more seriously, and denounced the frat boy uniform that so many people my age have adopted. I’m doing my part…

Good Lord, Sart, you’re really trying to get on my good side with this delicious photo, aren’t you? I love everything here: the DB blazer, checked shirt, skull-and-crossbone slippers, pocket square. To me, the best thing about the pic is the hair. The hair on these gents is superb. Okay, their sideburns are a tad bit long. But aside from that, they are to die for. Magnificent.

Call me old fashion, but I’ve never been a fan of worn jeans, especially on myself. But I must say he pulls them off very well. At first glance I thought he was going for the pirate look, then I looked closer and saw his slippers and then I knew it was the pirate look.

I don’t understand, Sart… I normally agree fully with anything you say, or at least I understand where you’re coming from, but I think this looks utterly ridiculous.Let’s start at the feet- the shoes look like children’s slippers. The skull is silly looking. I may understand a little better if it was a crest, but that isn’t even Alexander McQueen looking… it’s Bloomingdales kids pyjamas, for ten year olds wanting a bit of Jack Sparrow in their neightwear.On top of that, so much bare ankle and foot from the low front of the shoe and the rolled up jeans makes it look unfinished, as though he has slipped on the shoes in the dark to leave the house in haste.The jeans just seem too blue and too contrived. They do not look like real worn denim, they look light purchased yesturday ‘distressed look’ denim, and I do not believe that the jeans go with the jacket- their wash and wear is simply too casual for the formality of the jacket. Perhaps slim fit indigo jeans may be more acceptable, or a similarly more formal denim, but this casualness with the formality is a juxtaposition so awkward and contrived looking that i’m just cringing at the sight!

I’ve got quite a few Polo/Black Label jackets. There’s something rather comforting about wearing double breasted jackets, or more military inspired looks.…..no doubt because the state of world affairs.

Funny how I couldn’t really imagine my husband wearing this look, but I am personally trying to figure out how I can create a similar look for my self. I think I would do a pair of MaryJane shoes, darker jeans and that perfect big Cole Haan chocolate brown bag I am praying for and lastly a 1930-40 hair style.

Those Purple Label slippers cost an arm and a leg (retail is over $1k after tax). Seems a lot of people don’t get the look at all, but I think it’s very cool. It absolutely captures the essense of RL PL as a brand. I was wondering if there’s a particular name for the look?

I love it, I think he is trying to be a little contrived, and he’s pulling it all off. I find it a little humorous, perhaps that’s the angle? I love the skull on his loafers. I want to see what the guy he is speaking to is wearing too.

And thanks Sart, your right, sometimes it just takes a slightly different perspective on your own wardrobe to freshen up the way you wear it.

As a long time East Coast transplant to SoCal I have to say Bravo! Bravo Sartorialist! This is a perfect look for the preppy in all of us out here on the left coast – I will be doing my take on this look next week.

Way east-coast waspyâŠit’s a cultural thing, evidently.The bag should be as tattered as the factory distressed jeans. It looks as if he’s trying to pull off an American East meets West look. Real 501s or navy dungarees might have worked better here. Heck, he should’ve rolled the pants almost up to his knees!

The slippers Rock!! Very rebellious with the skull & bones. If I had to bet they are Purple Label. He looks good. But let's talk about the guy in the trench. I'm guessing he has a great pair of engineer boots on with those selvege denim. He looks almost just as cool.

Seeing how I know very little about mens clothes, feel free to disregard my comment. However, I find the patches on already far too treated jeans especially distracting paired with that exquisite jacket. Despite that, it’s still an inspiring look.

To be quite honest, what speaks to me the most in this post is the last paragraph you typed. “It sounds so simple…mentally reorganize my closet.” Well said!

But when I saw this picture, it makes me think of the selection I have left after putting off doing my laundry. I just have odd pieces that people wouldn’t normally wear together but I wear anyway because…well, it’s either that or go starkers!

Seems so very contrived. One of the pleasures of most of your photographs is that although I know thought has gone into them, they seem artless and casual. As if the subject has more on his/her mind than wowing me with his good taste. Not so here.

And again, no older women? During Fashion Week in NYC: no women over 30 dressed with panache and style?

I love his look from the waist up. The jacket is lovely. The pocket square works wonderfully with the color of the shirt. His hair looks sharp. The rolled cuffs on his jacket and shirt show some individual style and that is great.But, the jeans are a mistake with this outfit. The other guys around him are all dressed for business. The tattered jeans just don’t work in this setting, nor do they work with the formality of the navy blazer and pocket square.The velvet slippers are whimsical. I think that the slippers would work if the pants were more traditional.

Great look, last seen by me on 16 year old Italian, minus the slippers sheltering from a late summer storm in Cortona. He had Clark’s chocolate desert boot on.

The rolled cuff, and over sized watch isn’t unusual in Italy. If you live in a tiny apartment, and spend most of your salary on bespoke, (unlike the English) you want more than your tailor and bank manager to know about!

Good see velvet slippers getting another airing… a true vestage of 80′s London jazz dancers (Tricker’s of course).

I love this guy, and what does it for me is the fun he is having dressing up. Rules are great, but the best ones are those you make up yourself!!

Scott, it sounds as if you took the negative comments on this photo a tad too personally — why the cringing? — it’s just someone’s fashion/style opinion on a single outfit — nothing more or less than that — not some personal evaluation of his character or goodness. It’s really about the fashion/style choices he made that morning as he was putting the look together — some people liked those choices, others didn’t. But I hope you continue to allow those who happen to differ from YOUR fashion/style choices to comment on your wonderful blog…

i agree with a few others in being against buying torn jeans.. the flipped-up sleeves look fantastic.. and i really want some suede loafers!

what about the rolled jeans look? i’ve been doing it with some jeans that i bought overly-long for a certain look when theyre not rolled, but now to cuff them two or three times they are still touching my shoes and i feel like a pirate.

I usually agree with Mr. Sartorialist but this is one of the most ridiculous looks I’ve ever seen. Torn jeans with ultra nice jacket and pocket square and – get this – velvet slippers? Give me a break. Such a look only makes sense if one is trying to show one has put attention into what one wears, like at a costume party or something.

SART, Not sure you will post this as I have noticed quite a heavy handed censorship when there is disagreement. I would hope this excellent blog does not risk being a new agey ultra positive site and stay the course with sartorial discourse. Sparing someones feelings should not be an option. That being said… This outfit…Yuck. I use this word as my previous post never made it so I will go down a couple rungs. Peace

We understand that you’re partial to this look. That’s one of the reasons I didn’t comment, though I felt the urge to. It seemed unnecessarily hurtful to express my own response to a look you championed as perhaps your favorite look of the season.

Not that you or the look needs protection, but it just seemed an unnecessary step. I’ve learned the cost of glib negativity, here, and to myself.

I commented negatively once about an outfit I disliked (I was Hungry Eye, and it was a post of a man dressed in a black blazer and black jeans) and you came on and reprimanded me for it: “Do you have no sense of texture?”, etc…)

I felt horrible all day (I was chewed out by The Sartorialist!) and I realized I’d been unnecessarily cruel about a real human being, projecting and venting maybe some of my own issues on this man in the no-repurcussions zone of the blogosphere.

I apologized and I’ve been Anonymous and POSITIVE-ONLY ever since.

Others obviously felt no such delicacy here. But the fact that you came on to chastise them disturbs me. Do you only do that when you identify personally with a look on a man?

Nobody has said anything bad about the man himself here. You didn’t step in to defend the guy in fishnets recently, though commenters to that post went much further in attacking that man’s actual character, sanity, and body shape.

Here, they just attack his look, and the overall response is more positive than for many posts.

Maybe you should lay some ground rules, like: we’re not allowed to get too specific about what we like and don’t like about a particular look if it’s a look The Sartorialist is particularly fond of or identifies himself with.

Or maybe stop posting comments altogether that do anything other than take each look for its “positive inspiration”.

That way, we’ll have to work harder, be more imaginative, and the comments section will be less a collection of easy personal prejudices and more of a fun game.

The slippers look to houseslipperlike. And I’m not a fan of skulls at all. But I think he did a fantastic job combining two extremes. The jeans I wouldn’t have rolled up because it makes him look smaller. If he would’ve worn a more classic pant he would’ve looked like an old fuddy duddy, but he balances the jeans greatly by combing his hair to perfection! Overall a great looking guy!

for the sartorialist… It’s a fine line between criticizing people for being themselves and criticizing fashion. I’m with you on respecting people for being themselves, though I had serious problems with this outfit, which collided with my satirical sense of humor.

I despise truisms like: older women should not have long hair, men shouldn’t push up their jacket sleeves, fancy jackets don’t go with jeans, etc. And if someone dares to dress imaginatively, sometimes they’ll fail aesthetically and even look foolish, at least in some eyes, but it’s fun and inspiring and admirable anyway.

hey man it’s all about style and if you don’t have it you don’t have it. that’s all there is to it. i see people with great clothes but they just don’t seem to know how to put it together so it doesn’t matter what label or how much money they spent on their wardrobe they still can not achieve that look. now the people with style even though the clothes they have on are just plain ugly because they are part of the equation the outfit looks amazing. it has to do with ” je ne sais quoi”. this guy with the double breasted jacket has it and even if put he puts on sweat suit he still looks good.

The thing is, Sart, he’s not “being himself”…he’s totally drunk the RL Kool Aid. Honestly, he’s wearing Mr. Lauren’s idea of what to wear for what–sailing to the opera, and maybe stopping off for a little gardening…would he be wearing that get up if he were a VP of Gucci or Zegna?

Maybe this isn’t all sunshine and rainbows, but I’ll say it anyway. Are Manhattan’s elite so divorced from the reality of breaking in clothes that they need to buy things that are fake-distressed? Rhetorical question.

I have jeans with holes and patches that came from my clumsiness and I have the matching scars on my knees, legs, etc. to prove it! And I’ve worn them enough so they fit me well and conform to my body.

That being said, if there was less of a contrast between the blazer and the jeans, I think the outfit would work better. If the blazer were less formal, the outfit would be more streamlined. Or, if the jeans were not tattered, the blazer would look less severe.

You people all need to get a life and stop waisting it commenting on other’s manner of dress. It must be pretty easy for you all to disparage these people annonomously. Wouldn’t you love to know what people think of your fashion sense on a day to day basis and have your personal style scrutinized. How fun! How human!

Yeah I’ve been cutting about Glasgow like this myself for the whole summer…it’s an ambitious look for Scotland! Like others here I’ve worked the look up from existing pieces in my wardobe. I’m not sure about the slippers.

I have said before that you dont have to agree with the choices but you have to be respectful of how you write those feelings. There are plenty of negative comments written in most of the posts but they are usually written with some amount of respect. This is not a place to make people wrong for their choices.

this particular post had lots of comments on what people THOUGHT this gentleman might be like – just look at “aitch” post, lots of speculation about this person that “aitch ” could never possibly know.

Moderating comments is not an exact science. If you want a “guideline” how about – if you wouldn’t say it to their face then don’t say it here.

Sartorialist, Thanks for your comments on commenting and moderating. I’ve had comments censored by you and was never upset by it, in fact I often figured out why the comment “didn’t make it” and ended up being grateful to you for not posting it. “If you wouldn’t say it to their face…” is excellent advice and easy to remember.

Well gang… I work for the guy in the picture and although his is not my style of dress – I must admit he has a splendid aesthetic and actually does live the lifestyle he represents with his clothing ( not to mention he really is a terrific guy to work for).

The nature of being avant garde is to please and delight those who are cutting edge while distressing or confusing those who are less enlightened. I will play my part by admitting to being distressed and confused by the combination of this flashy double breasted jacket with distressed jeans. I love the jacket and especially the pocket square but I hate them with the jeans.

In the right circumstances the distressed jeans may have a certain sex appeal. It suggests a artist, gardener, or other creative person — caught in the act of the physical creation. But together with the jacket, the look is too contrived for my taste.

the look is oh so exaggerated. preppy + italian..oh god!ha! funny how I am too keen on such visual reminders. bravo Sartorialist. I do something similar, just in Rome, where I live. Just haven’t set up shop [blog] yet.baci-Balticeyes (marta)

The fashion patches and tears in the jeans are very nice finding real vintage jeans like these would be very cool but also much harder to aquire its all about the early 1900s; the faternal skull image and the gussets in his shirt that he should have. Great!God save Ralph Lauren.

Not so crazy about the loafers. But the rest of the looks is okay. Am wondering what elements could have been tweaked a bit to make it look like it wasn’t trying so hard. Not sure. Maybe if he had messy surfer hair and had paired with a pair of tattered vans –I’d of been charmed.

it would be inetresting for you sart to make all commentors post a picture of themselves of what they are wearing and open to comment from others then we would see how little those negative comments would become. While eveything in this ensamble may not be to my stylistic liking, it takes great courage to be dressed like this in NYC, in London not, for there is that individualistic thing that one finds only here.As SVP at RL this man represents the brand he works for 1000%.The aspriational WASP,as newly poor.Im sure it is look that will catch on with Lehman brothers and AIG ex employees.How of our times this shot is when times are bad stick to the classics.

Hi. Love your site. Your photography is done with the “special” eye. And you get the looks. All are fair, and none to be disparaged. I was surprised by your comments on the look, however. This is quite an old look, in prep school circles. I wear DB Burberry Navy with 501′s all the time, and pair them with cordovan Aldens, or fabric or corded suede loafers. I especially like cordovan Monk Straps from Alden. Seems natural. The boy needs to lose the overdone jeans. Jeans are appropriate, so long as they are appropriate. This is like the Santa Fe Aston Martin covered with good New Mexico mud, for effect…. melodrama.

I like the contrast of country club formality pitted against the tattered jeans- it may feel contrived to some, but at the same time, it also feels very real to me. Looking at it through the lens of a "Ralph Lauren" look, it's a great blend of Double RL workwear and the classic Gatsby/collegiate WASP look of Polo. I did a similar look (independently of seeing this picture) with a tailored tweed jacket and vintage WWII chinos that have actually been worn-out at the knees and have real paint splatters. I don't know if that makes it any more authentic…it's not like I fought in WWII. But I was on my knees painting. For many on here, it seems like there's a cultural reference confusion. Clearly, A&F torn jeans and pirate movies are too fresh in our collective memories to look at this as something inspirational or dare I say it, rebellious?

And I would have to agree that some people commenting should use some manners when they have strong feelings about a certain look…something that anonymity on the internet has made people forget. These are real people, and a lot of the people that have been featured on this blog are also avid followers of it. I like that the sentiments voiced here are unbiased and real opinions, but at the same time, would you repeat the same sentiments in the same way to that person to their face in real life?

Best regards to all fashion critics-amateur and professional alike,

Ray Chu (aka "the kid in the too tall fedora and bulbous shoes" from a few months back)

this guy is one of the consistently best dressed people at 650 Madison. he is one of the key creatives at Polo and really brings it on everyday in terms of the style quotient – personally and in his job. what is striking is that the depth of knowledge in terms of classical menswear is so deep and nuanced that when he plays with the references, it looks so fresh, impeccable and “right”. Ralph has a small army of creatives like him who all put their unique stamp on Polo. its what keeps the brand so relevant.

who are those slippers by?? i’ve seen those on a very stylish lady in London (she was wearing them with white opaque tights and a kilt printed red dress, it looked very cool!!) not too long ago and it immediately added something to the outfit and the persona… but you have to know how to pull them off!

When I get married I want my husband to look exactly. like. this. A nice meeting point between Brooks Brothers and L.L. Bean. Perhaps the true prep didn’t die with the 80s. It also looks like he is wearing Stubbs and Wootton slippers, one of my longest lasting fashion obsessions. Even if you don’t summer in Nantucket doesn’t mean you can’t dress like you do… -Camille